How My Crossdressing Trip Begun

Even though some of us are quite used to crossdressing, and see it as a natural thing, we all had to begin somehow. For the vast majority, it wasn’t an easy process. Lack of confidence and acceptance can keep us away from crossdressing, and make us struggle with our expression. It’s a common issue, but each crossdresser has its own journey. And today, my goal is to tell you how I went through mine. My case wasn’t any particular challenge or something to brag about. But I do think it may bring some hope and inspire other crossdressers to be themselves.

I’ll try to tell you as much as possible, in order to give y’all a better view of the whole process. From the days I started to question my gender identity, at a young age, to my final acceptance and coming out. It involves a period of self-doubt, a long process of understanding, a slow one of building confidence. It was, however, very rewarding in the end and I’m more than glad to share my experience with my crossdressing sisters.

In order to organize it in an understandable way, I’ve separated this article into a few sections. This way, I can properly write about the events that took place in each phase of my journey. They complement each other, as book chapters do to a story. Anyway, this is how my crossdressing trip began:

1. Years of questioning my gender

This was at a very young age, during my days at primary school. I didn’t have anything against dressing up as a boy, but I felt it wasn’t enough somehow. I couldn’t express myself completely, I was missing something, but I didn’t know what it was yet. It wasn’t until I saw the movie “white chicks (2004)” that the penny dropped. I was thinking something like “hey, I would like to do that!”, and I finally started to understand what I was missing. A few years later, I was trying on some female shoes and lipstick hidden from everyone, even a dress when I was 5 or 6 years old. I guess I can say it was my first gender-questioning experience, and I kinda stopped for a while after that.

I thought to myself that I was just confused and lost, but I still felt that desire to dress up as a girl. Even if I didn’t feel like a female 24/7, I knew I had to do that someday. By this time, gender ideology wasn’t very well spread in my country, and people rarely talked about it. I used to hear conservative relatives making fun of trans people, with ill-intentioned jokes. This kind of situation made me very afraid of coming out, as I thought my family wouldn’t understand what crossdressing was. Well, at this point, neither did I.

Not knowing what I was, made wanting to crossdress something very painful to me. I wanted to do something I both didn’t understand and was afraid of. I remember watching some reports and occasional documentaries about trans people on the TV, and thinking “I wish I was trans, but not all the time”. It sounds funny nowadays, but it’s a good representation of how I was feeling, unable to figure out my own gender.

2. The problem of self-doubt

All this misunderstanding led to a lot of self-doubts as well. I guess this is a common situation for most beginners in terms of crossdressing. Sure, I wanted to dress up, look and sound like a girl, but I was afraid I couldn’t. I was 14 years old and puberty was starting to hit me, with facial hair and other masculine features developing. However, I hadn’t started to grow in height and was quite chubby. I wouldn’t call myself ugly, but I wasn’t attractive either: something the girls in my school would make very clear. On the other hand, while I thought them to be attractive, I felt gender envy more than anything else. With a few exceptions, I couldn’t develop romantic feelings for them as they were quite mean, but I wanted to look like them so bad…

This huge gap between what I looked like and how I wanted to present myself as an enormous blow to my self-esteem. I was let down by my own appearance, and as the pessimistic teenager I was, all hope seemed lost. I did all I could to neglect my crossdressing side, but it wasn’t great for my mental health. I felt sad, incomplete, and that I wasn’t being true to myself or to the ones I love. Somedays, all I wanted was a wig and a dress, and I felt that it would make me the happiest person in town if I could get them. Every time I had this kind of thought, I tried to repress and ignore it, but it wasn’t working.

The only “exhaust port” I found for this feeling was video games. I would frequently create female characters, and present myself as a girl online. I kept a low profile and avoided anything that could link me to such characters, frequently creating new emails. Eventually, I felt overwhelmed by all the effort I had to put into hiding it, so I stopped. Once again, I was denying my own nature, feeling upset and insecure as a result. Could I ever be myself? Could I ever look feminine enough? Such questions would follow me all the time. That’s when everything changed (for the better, of course).

I was once watching a speech at school, and they were open to questions at the end. I had one, so I raised my hand and waited my turn. What happened was that I was misgendered, and they called me “that girl over there”. Well, I had long hair, which may have contributed to that, but I was happy nonetheless. If someone mistook me for a girl even without makeup and proper clothes, how feminine would I look if actually tried? That’s basically how I stopped repressing this side of my personality and accepted that I could be a girl sometimes.

3. Understanding what crossdressing is and finding out my gender

By the 2010s, people, where I live, were showing a more respectful side. Gender ideology was more openly discussed, and LGBT people were coming out with confidence. However, it wasn’t until 2015 that I first heard the word “cross-dressing”. Once I was no longer neglecting and repressing my girlish side (at least for myself), I wanted to learn more about it. My search history included entries such as “how to do MTF makeup” and “how to disguise myself as a girl”, as I didn’t know how to write it down. Not too long after, I found a few videos titled “crossdressing tutorial”, “crossdressing makeup tips” and such. I looked up the term and finally understood what I was trying to learn.

During high school, I learned a lot more about crossdressing and gender identity. I used my free time to watch videos on the subject, and learn new skills. I made a list of stuff I wanted to buy, but I wasn’t making any money by myself, so I knew I had to wait. I don’t know how, but I managed to be quite patient. My list included a variety of wigs, different skirts, makeup supplies and shapewear. It also included bodysuits and breast forms, since I had already heard of Roanyer and this kind of thing.

After that, it didn’t take me too long to figure out my gender identity. I felt that I was ok with presenting myself as male most of the time, but that I preferred to be seen as a woman on other occasions. I knew about the terms “bigender” and “nonbinary”, but they didn’t seem to fit me properly. But then someone told me about the gender-fluid identity, and it felt just right for me. I don’t like labels, but I felt I was okay with that one, and that’s how I see myself nowadays.

4. Self-acceptance and coming out to my girlfriend

By the end of high school, I knew precisely who I was. Yet, I still lacked the confidence to come out and crossdress in front of other people. Besides the occasional underwear and makeup, I didn’t dare to buy a wig or other stuff that would be hard to hide. I was dating my current girlfriend for about a year, and I decided I could trust her. And so I did. A thing we both like is to cosplay our favorite characters from pop culture. Then, I first told her I wanted to cosplay a few female characters, and that “gender” was restricting my creativity. She was cool with it, and a couple of months later I told her it wasn’t just cosplay.

I explained how I felt, and how I identified as a gender-fluid person, and she couldn’t be more comprehensive. She helped me with makeup, and to shop for new stuff. She was with me when I bought my very first wig and taught me how to hide it. I started to crossdress on a regular basis with her by my side, and my self-esteem saw a massive increase. I finally felt that I was being my true self. I regard this as the actual beginning of my crossdressing trip, with enough knowledge, support and confidence.

Even though society imposes a lot of barriers for crossdressers, it’s still possible to find hope. I know everyone has their own life and context and struggles with different things. But my goal here was to provide an example of how things can turn out well for us. My story is far from finished, and I’m living my own life. Even though the experience I had until now may be helpful to someone to a certain degree.